Dorothy grew up in the 1950s-60s when most mothers were homemakers. She enjoyed Nancy Drew books and detective shows as a child but didn't consider being a detective as it was uncommon for women. As an adult, she was the first black female parole officer in Illinois and later investigated corruption in the prison system. She found providing security for famous musicians interesting and enjoyed conversing with Smokey Robinson. Dorothy stresses the importance of communication skills, computer research, adapting to changing situations, and blending in undercover for aspiring detectives.

1. NMG: When you were a girl, did you ever think you would
grow up to be a detective?
Dorothy: During the 1950s and 1960s when I attended grade
school, all the mothers on my block were homemakers. They
raised the children, cooked, cleaned, and volunteered at the
PTA and elsewhere. My father did not believe that women
should work at jobs or wear pants—can you imagine that?
The only female I knew who worked outside the home was
my Aunt Ruthie, who was a nurse at the hospital. At the time,
I thought I would be a nurse like her when I grew up.
I remember that when I was around 11 or 12, the books that
interested me the most were the Nancy Drew mystery books.
And I remember loving to watch all the “who-done-it?” shows
on TV such as “Dragnet” and “Perry Mason.” I knew what
a police officer did, but I never thought of a female doing that
type of work.
NMG: What did you enjoy most about working as a parole
agent and internal affairs investigator?
Dorothy: I liked talking to people who had gotten out of jail
and encouraging them to change their lifestyle and stay out of
trouble. (I only worked with women until 1975, when equity
laws allowed women officers to work with male parolees as
well.) I had to
listen to them carefully, because some were drug users and
others were still used to their former life of doing illegal things
to stay alive and have food on the table for their family. This
helped me learn about “life on the street,” which was useful for
me in my detective work.
In my internal affairs work, my job was investigating anyone in
the state corrections department (the prison system) suspected
of any crimes, such as taking bribes from prisoners and “getting
caught with their hands in the cookie jar.” It was hard because
no one likes the person who does this, but it also taught me
skills that came in handy later.
NMG: What parts of these jobs were the most challenging or
scary?
Dorothy: The most challenging part was proving myself almost
daily to be taken seriously. As the first woman and first black
person hired, I always felt an unspoken but visible “we don’t
want you here” attitude from a lot of the men I worked with.
As a female, you couldn’t just be average like many of the other
men—you had to prove yourself above average. The attitudes
did start changing after the first time I pulled something off that
was not only good, but outstanding!
As for the scariest, some might think I would list all the
unannounced raids at prisons or picking up prisoners for
transport or when I interviewed Richard Speck, who killed
eight nurses in Chicago. But it actually happened one night
when I was serving parole papers to someone who worked
a night job. I was walking down an alley on the west side of
Chicago; it was very dark and I thought I better take my gun
out. I heard a noise and pointed toward it ready to shoot before
I saw that it was a cat. I made myself a promise right then to
never draw my gun while walking—what if the cat had been
a child playing? I decided I would fight first if something came
up. My dad taught me early on to fight and wrestle, and I was
good at it.
The Nazis considered
her “the Allies’ most
dangerous spy.” And yet they never
captured Virginia Hall, an American
woman who armed and trained
French battalions to do sabotage,
planned countless missions, and carried out
undercover operations as a journalist and milkmaid. And
she did all of this with one wooden leg! In this painting,
Virginia transmits secret messages from her suitcase
radio, powered by a bicycle wheel.
Herstory!
Dorothy (above) doing surveillance
work; center, her pile of disguises
Detective Dorothy Wesley likes to bust barriers. Starting out in
law enforcement, she was the first black female in Illinois to be an
adult parole officer, and she was the first female assigned to a special
prison corruption investigation unit. Then she was one of the few females
providing security to famous entertainers. Now she’s the first black woman
to own her own private investigation firm in Delaware. Dorothy shares
awesome advice for aspiring private eyes—thanks, Dorothy!
Meet Private Eye Dorothy!
Women’s Work
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16 new moon girls • www.newmoon.com • November/December 2014

2. NMG: What was it like to provide security for famous
entertainers?
Dorothy: It was so interesting to be around people such as
Michael Jackson (when he was part of The Jackson 5), Johnny
Cash, Chaka Khan, and others. I was asked to work for Donna
Summers—I said no—but I went to the movies with her and her
party. Dolly Parton is as sweet in person as she is on stage, along
with Sarah Vaughan and James Brown. My favorite was Smokey
Robinson, who wore a cross under his shirt. We got to have a
conversation about God.
NMG: What skills are most important to develop for girls who
are interested in being detectives?
Dorothy: Don’t ever hesitate to ask more questions. There is no
such thing as a stupid question, and the question you may decide
not to ask could be the one that will break a case. And when you
have learned a lot, share your knowledge with others just starting
out as you once were.
Communication skills are very important—you need to know
how to listen well, and know when and how to talk. Take speech
classes to develop verbal skills. Sometimes you’ll need to switch
stories quickly to get the information you need. You need to
know how to be an “actor”—for example, you’ll need to develop
a “poker face” so that your emotions don’t show when talking
with a person. You also need to be able to read other people’s
emotions. Their body language and the way they talk will often
say much more than their words.
Computer research skills are very important. You’ll need to find
out all sorts of information quickly, and be able to understand
complicated laws concerning a case. You’ll need to keep up
with the latest gadgets for videotaping and recording and other
surveillance.
You also should have a good sense of knowing your surroundings
and how to change plans quickly. For example, if I’m following
someone, I need more than a GPS. I need to know about roads
that are parallel to where the suspect is driving so I can end up at
the same place ahead of him.
Of course, if you’re going to do spying undercover, you’ll need
to know how to dress in ways that blend in, and also be able to
change “identities” to confuse others. You have to literally “wear
many hats” in my business—I own over 100 hats!
When you get started in the private investigation business,
you will find out if you enjoy the work, or if you would like
something related to it, such as being a police officer or working
for the FBI or CIA. If you work at something you love doing, you
will never think of it as work. After more than 40 years as a PI, I
still get a rush every time I solve each case!
When Mexico wanted to
stop being a colony of Spain,
Josefa Ortiz de Domínguez
quickly joined in. She had long
hated the cruel treatment of
indigenous and mixed-heritage
people by Spanish rulers. She
organized secret meetings and missions
that led to the Mexican War of Independence.
Herstory!
Being a
wireless
operator who
transmitted
secret
messages was
highly dangerous
in WWII, but Noor Inayat
Khan left her privileged life
to do her part. She was a
Muslim pacifist, and wanted
the war to stop. After
someone betrayed her, she
was captured at age 30, and
executed at the Dachau
concentration camp.
Herstory!
After Lydia Barrington Darragh came to the American colonies from Dublin,
Ireland, she married, bore 9 children (only 5 survived infancy), and worked as
a nurse and midwife. Amid all these responsibilities, she took on the cause
of the American independence struggle. When the British military leaders
made their Philadelphia headquarters in the house across the
street from Lydia’s home, Lydia started spying for General
George Washington’s army. She carefully conveyed her
info in coded messages. And when the British troops
demanded that Lydia’s family house British officers,
Lydia readily agreed, and eavesdropped on
important conversations. When she learned of a
planned surprise attack on Washington’s army,
she set off walking through the snow to deliver
the news. The American troops were now
ready for battle and defeated the British. Lydia
had helped win the American Revolutionary
War!
Herstory!
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